Alan runs into Cynthia, a mutual friend of he and Judith from back when they were married. Cynthia is recently divorced and Charlie gets that vibe that Cynthia might be interested in Alan. However, Alan is unsure about asking Cynthia out because he knows she's still really good friends with Judith. He gets Judith's blessing and sets up a date with Cynthia. Charlie tells Alan that he is so going to get laid tonight� "You've been friends for years, what more do you need to establish? You best bring your "A" game because you know she's going to go back and tell Judith about it."
Pre-sex and in bed Alan is really worried and starts seeing images of Judith sitting on the chair next to them in bed. Alan does his best and Cynthia is more than satisfied. He asks Cynthia to tell Judith that he was remarkable in bed. The next day in his kitchen he debriefs Charlie on last night's events but seems a little distracted, almost bummed out. He's being seeing visuals of Judith and Herb making love and Herb is better than Alan ever was with Judith. While on a date with Cynthia, Alan keeps on questioning her about what Judith says about her lovemaking with Herb. What makes him so good? Annoyed, Cynthia dumps Alan claiming that he still has feelings for Judith.
The show's 100th episode ("City of Great Racks") aired on October 15, 2007. To celebrate this, a casino-inspired party was held at West Hollywood's Pacific Design Center. Warner Brothers Television also distributed blue Micargi Rover bicycles adorned with the Two and a Half Men logo along with the words 100 Episodes. Each bicycle came with a note saying "You've made us very proud. Here's to a long ride together." The cast also gifted the crew with sterling silver key rings from Tiffany & Co, the key rings were attached to small pendants with 100 and Two and a Half Men inscribed on either side of it.